Structure, synthesis, and applications for oligo phenylene ethynylenes (OPEs)

Abstract

The present disclosure provides novel oligo phenylene ethynylene (OPE) compounds, methods for synthesizing these compounds, and materials and substances incorporating these compounds. The various OPEs show antibacterial, antiviral and antifungal activity.

What is claimed is: 
     
       1. A material incorporating an oligo-(phenylene ethynylene), wherein the oligo-(phenylene ethynylene) is grafted thereto by chemisorption or wherein the positively charged polymer attaches to a negatively charged surface by physisorption, wherein the oligo-(phenylene ethynylene) has the structure: 
       
         
           
           
               
               
           
         
         wherein:
 n is selected from the group consisting of 1, 2, 3 and 4; 
 A is selected from the group consisting of C 2 C 6 H 2  and C 2 C 4 S; 
 B=C 2 C 6 H 2 ; 
 C=is either C 6 H 4  or not present; 
 X is selected from the group consisting of: COOCH 2 CH 3 , O(CH 2 ) k N(CH 3 ) 3   + , O(CH 2 ) k SO 3   − , and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 ; 
 Y is selected from the group consisting of: COOCH 2 CH 3 , O(CH 2 ) k N(CH 3 ) 3   + , O(CH 2 ) k SO 3   − , C 6 H 2 (OCH 3 ) 3 , and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13   2+ ; 
 k is selected from the group of whole numbers from 1 to 10; 
 Z A  is selected from the group consisting of H and O(CH 2 ) j (C 6 H 12 N 2 )C 6 H 13   2+ ; where j is selected from the group of whole numbers from 1 to 10; and 
 Z B =H; 
 
         wherein:
 if X=COOCH 2 CH 3  and Y=COOCH 2 CH 3 , then A=B=C 2 C 6 H 2 , C is C 6 H 4 , and Z A  is O(CH 2 ) k (C 5 H 12 N 2 )C 6 H 13   2+ ; 
 if Z A  is H, A is C 2 C 6 H 2 , X=O(CH 2 ) k N(CH 3 ) 3   + , and C=C 6 H 4 , then Y is selected from the group consisting of COOCH 2 CH 3 , O(CH 2 ) k SO 3   − , C 6 H 2 (OCH 3 ) 3 , and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13   2+ ; 
 if Z A  is H, A is C 2 C 6 H 2 , X=O(CH 2 ) k N(CH 3 ) 3   + , C=C 6 H 4 , and B=C 2 C 6 H 2 , then k is selected from the group consisting of 1, 2, 4, 5, 6, 7, 8, 9, and 10; 
 if Z A  is H, A is C 2 C 6 H 2 , X=O(CH 2 ) k N(CH 3 ) 3   + , and C is not present, then Y=C 6 H 2 (OCH 3 ) 3 ; 
 if Z A  is H, A is C 2 C 6 H 2  and X=O(CH 2 ) k SO 3   − , then C=C 6 H 4  and Y=O(CH 2 ) k SO 3   − ; 
 if Z A  is H, A is C 2 C 6 H 2 , and X=O(CH 2 ) k (C 5 H 12 N 2 )C 6 H 13   2+ , then C=C 6 H 4  and Y=O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13   2+ ; 
 if A is C 2 C 4 S, then C=C 6 H 4  and X is selected from the group consisting of O(CH 2 ) k N(CH 3 ) 3   +  and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13   2+ ; 
 if X is O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13   2+ , then Y=O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13   2+ ; 
 
         wherein both the oligo-(phenylene ethynylene) and the material incorporating the same have biocidal, antiviral, and antifungal properties. 
       
     
     
       2. The material of  claim 1  wherein Z A =O(CH 2 ) j (C 6 H 12 N 2 )C 6 H 13   2+ ; A and B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=COOCH 2 CH 3 . 
     
     
       3. The material of  claim 2  wherein j=3. 
     
     
       4. The material of  claim 1  wherein A and B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=O(CH 2 ) k N(CH 3 ) 3   + . 
     
     
       5. The material of  claim 4  where k=2. 
     
     
       6. The material of  claim 1  wherein A and B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=O(CH 2 ) 3 SO 3   − . 
     
     
       7. The material of  claim 1  wherein A=C 2 C 4 S, B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=O(CH 2 ) 3 N(CH 3 ) 3   + . 
     
     
       8. The material of  claim 1  wherein A and B=C 2 C 6 H 2 , C is not present, X=O(CH 2 ) 3 N(CH 3 ) 3   +  and Y=C 6 H 2 (OCH 3 ) 3 . 
     
     
       9. The material of  claim 1  wherein A and B=C 2 C 6 H 2  and C=C 6 H 4 . 
     
     
       10. The material of  claim 1  wherein A=C 2 C 4 S, B=C 2 C 6 H 2 , and C=C 6 H 4 . 
     
     
       11. The material of  claim 1  functionally attached to a material or substance so that the oligo-(phenylene ethynylene) can interfere with the pathogenicity of a pathogen that contacts the oligo-(phenylene ethynylene). 
     
     
       12. The material of  claim 1  where k=3. 
     
     
       13. The material of  claim 1  wherein the material is a fiber, or a textile formed therefrom. 
     
     
       14. The material of  claim 13  wherein the fiber or textile comprises a natural fiber, a synthetic fiber, or both. 
     
     
       15. The material of  claim 14  wherein the natural fiber is cotton, silk, or wool, or a blend thereof. 
     
     
       16. The material of  claim 14  wherein the synthetic fiber is rayon or nylon. 
     
     
       17. The material of  claim 14  wherein the synthetic fiber is produced by electrospinning. 
     
     
       18. The material of  claim 13  wherein the fiber or textile is comprised by an object that is potentially contaminated with a microorganism or a virus. 
     
     
       19. The material of  claim 18  wherein the object is a wound treatment, a bandage, a swab, a sterile mat, a liner, or a filter for water purification. 
     
     
       20. The material of  claim 18  wherein the object is a mattress, a bed linen, a countertop covering, a tablecloth, or a curtain. 
     
     
       21. A material incorporating an oligo-(phenylene ethynylene), wherein the oligo-(phenylene ethynylene) is grafted thereto by chemisorption or wherein the positively charged polymer attaches to a negatively charged surface by physisorption, wherein the oligo-(phenylene ethynylene) has the structure: 
       
         
           
           
               
               
           
         
         wherein:
 n is selected from the group consisting of 1, 2, 3 and 4; 
 A is selected from the group consisting of C 2 C 6 H 2  and C 2 C 4 S; 
 B=C 2 C 6 H 2 ; 
 C=is either C 6 H 4  or not present; 
 X is selected from the group consisting of: COOCH 2 CH 3 ,  − O(CH 2 ) 2 N(CH 3 ) 3   + , O(CH 2 ) 3 N(CH 3 ) 3   + , and O(CH 2 ) 3 SO 3   − ; 
 Y is selected from the group consisting of: COOCH 2 CH 3 ,  − O(CH 2 ) 2 N(CH 3 ) 3   + , O(CH 2 ) 3 N(CH 3 ) 3   + , and O(CH 2 ) 3 SO 3   − ; 
 Z A  is H; and 
 Z B =H; 
 
         wherein:
 if A is C 2 C 6 H 2 , X=O(CH 2 ) 3 N(CH 3 ) 3   + , C=C 6 H 4 , and B=C 2 C 6 H 2 , then Y is selected from the group consisting of COOCH 2 CH 3 , and O(CH 2 ) 3 SO 3   − ; 
 if A is C 2 C 6 H 2  and X=O(CH 2 ) 2 N(CH 3 ) 3   +  or O(CH 2 ) 3 N(CH 3 ) 3   + , and C is not present, then Y=C 6 H 2 (OCH 3 ) 3 ; and 
 if A is C 2 C 6 H 2  and X=O(CH 2 ) 3 SO 3   −  then C=C 6 H 4  and Y=O(CH 2 ) 3 SO 3   − ; 
 
         wherein
 both the oligo-(phenylene ethynylene) and the material incorporating the same have biocidal, antiviral, and antifungal properties, and 
 the material is a fiber, or a textile formed therefrom. 
 
       
     
     
       22. The material of  claim 1 , wherein the material is a stimuli responsive material.